Challenge Me
by KayLind1
Summary: "If you love two people at the same time, choose the second. Because if you really loved the first one, you wouldn't have fallen for the second." That quote inspired Elena, drove her every passion- every word towards her one true target. Damon.
1. Chapter 1

Introduction:

They say that it all began with Elena Gilbert's buried passion for Damon Salvatore, but that would be argued by the one and only Caroline Forbes who wholeheartedly claimed. "It's just because I kept her up all night Stefan, why are you getting so irritated?" And her protective claim was correct, Caroline's constant complaining had in fact kept Elena awake until dawn- but when you're undead and your emotions are heightened- what else are you going to do besides complain about Matt Donovan's unexplainable behavior? Secondly, Caroline refused to believe that Elena had feelings for Damon. Elena had so much heart, where Damon had nothing but a black hole- according to Caroline of course and other reliable sources such as Bonnie Bennett and everyone else Damon had recently pissed off.

In all actuality Caroline's explanation started from the time Elena woke up from her long nap, to this very breaking point where Stefan was pacing back and forth cursing Damon and Elena for something so small it even seemed ridiculous to Caroline- the crown holder for the Miss Drama Queen pageant.

"What are you really mad about Stefan?" Caroline asked him once she could fit a word through his ranting. It surprised people how rational Caroline had become, she'd really matured in a matter of months since her transformation. Then again, that was expected after a tragic death such as her own.

"I'm liar Caroline!" He yelled as his face distorted into the face of a demon, "I lied and I don't know how to make it right."

She led the Mary Kay brush down her face allowing the powder to cool her olive skin, it covered every regret-every late night she had spent. It covered the constant worry, and even that hatred for someone she had never met. It covered the fear for her own heart's desires, and comforted her soft beautiful skin to the point where she looked just like the weak, fragile lady she was supposed to be. "Yeah, Car', you were right new Revlon Aqua Powder feels just like water, and it wasn't just you." Elena found herself the center of Caroline's tests these days because of Bonnie's frequent emotional absences. Elena knew that Bonnie meant well, but she wished for only a second the once inseparable trio could be together without any vampire related chaos. Elena took a breath before she opened her mouth to speak again, "So what is the plan for tonight?"

"Okay, so I put a lot of thought and planning into this as you know. I texted everyone else a time to meet at the grill and the plans for the whole night. I'll text them to you now. " Caroline said cheerfully, "This is so exciting, I have been waiting for this night since I was in 8th grade and finally we're part of the upperclassmen slideshow!" Elena hadn't really focused on the slideshow or its famous awe, it never seemed to matter until Jenna died. Elena realized that one should never miss the little things in life that might change someone else's life. It was easy for Elena to regret the time she should have spent with Jenna before she died. Then there was Caroline, she did die- given she came back to life, she still died. This slideshow featured two parts of her life that are on two different sides of time. Alive and Undead constantly proved to be two separate things. "Okay, I sent it."

Elena walked over to her closet, pulling out a dress that still had tags on it. "What are you wearing tonight?" She asked Caroline, looking for fashion advice- that seemed normal enough. "Because I was thinking about this dress that I bought-"

"What does it look like?" Caroline asked before Elena could finish her sentence.

"You know- strapless dress that's longer in the back, it's made out of the like crochet lace material it has the skinny brown belt that goes around it…" Elena described it in the best possible way she could, knowing she was butchering the dress completely.

"The one you ordered two months ago." Caroline stated,

"Yeah, that one." Elena said as she eyed the dress in her closet, "You don't think it's too much for tonight?"

"No I think it'll look good for tonight, almost everyone is going to wear a dress." Caroline explained the classiness of the event tonight and how she was going to look her best. She then switched the conversation, "Is Stefan coming?"

"And Damon." Elena said with a smile although, she did not know why that made her smile.

"Why is Damon coming?" Caroline asked, Elena could taste the judgment in those four words as they echoed through her head. Why was Damon coming? Elena never seemed to have a reasonable answer for his constant presence. She just assumed everyone was used to it by now that she wouldn't have to explain it. But what she wanted the most was something that only had a slim chance. Elena wanted Caroline to know how much he'd change, although he could still be an ass… something had changed Damon's persona, and the angry animal look had vanished completely leaving a sad and mistaken lion in its track. She knew that he had her best interest in mind, and he meant no direct harm. And somehow, she felt something for Damon that she couldn't describe- she also felt pity for his heart. There were too many close calls to ever remove the scarring Katherine had caused.

Elena took a deep breath and repeated what she told Bonnie in an earlier but short conversation, "Damon's coming because he's worried about my safety. Plus, Stefan's going to be a little late for dinner tonight so Damon's stepping in to keep watch."

With much dismay from Caroline, they dropped the conversation and the night proceeded in orderly fashion- except one thing that caught Elena off-guard. Damon.

She heard his playful knock on the front door as she glided down the stairs in her white dress. "The door's unlocked." She said, rather than the casual term 'Come in'. She'd learned her lesson about the words to use, and not to use after a few close calls. Elena turned towards her kitchen as Damon entered with a smirk plastered to his face.

"If I knew this was a date, I would have brought flowers." Elena rolled her eyes at his comment, but it still made her laugh slightly. Damon toyed around with her family items as she pulled a sticky note off the blue pile on the counter. She wrote in very clear handwriting where she would be and what time she would be home, as well as emergency numbers such as Stefan's number, Damon's number, and the hospital numbers.

"I'm worried about him…" She explained to Damon, even though she did not have to elaborate on her steps of safety. He understood them perfectly.

Damon allowed Elena to lead the way to the door, she called out to Jeremy before she left. Elena yawned.

"Has Stefan been sneaking out of the house again?" Damon joked lightly, "I guess I'm going to have to ground him." His eyes shifted over to her flirtatiously. "Seriously, why are you so tired?"

"Caroline." Elena said, "She's upset about Matt and she wanted to talk about it."

Damon shook his head, Elena could only guess where his head was. "Barbie and Ken aren't enjoying the dream house life…" He muttered under his breath, trying to make Elena laugh again. This time she repressed her laughter- disappointing Damon. "We should leave before we have to hear about it from Caroline." He said those words, but at the same time his eyes said _let's stay._

Elena nodded her head, "Yeah…we should go." Maybe it was the reflection in her eyes that said let's stay rather than his. But, Elena never listened to her heart- everything was a sacrifice all the time. If she was willing enough to give up her life, she was willing enough to snuff out the flame of temptation.

They walked to Damon's beauty of a car, and he politely opened the door for her. "Careful." He said as she ducked her head through the door frame. Elena fell into the seat, and let him drive while the tension in the car wrapped around her head. The silence was overwhelming, but she didn't want to break it.

With Elena's parent's death, there became a fear where her future once harvested. It was a phobia to live life, or make any kind of choice that would prove to be horrible or prove to be the greatest thing in the world. The truth was she was determined to live her life in the middle, she didn't want extreme happiness because that would mean her parent's memory would fade- and she didn't want to be sad forever either.

"I see Caroline." Elena pointed to the blonde, "I'll let you park." She got out of the car faster than she ever had. Elena looked stunning, that was evident in Matt's eyes. She wished he wouldn't look at her like that. Yet, at the same time she was flattered by it.

Elena walked into the Grill with her friends, trying to distance herself from Caroline so she wouldn't start with the pestering questions. It failed as soon as they got seated at the booth. Elena faced the door so she could keep an eye out for Damon or Stefan. She doubted Damon would come anywhere near the table due to his low tolerance level for Matt, Tyler, and Caroline. Elena was surprised that Matt didn't pretend he had something to do. It had to be hard on him to see Caroline's friendly flirtation with Tyler who returned the favor with a double dose.

They created small talk that never reached the underlying subjects such as the vampires, the werewolves, and Damon Salvatore. They talked about school, and how this year felt really long but it was surprising to be so close to the end of it.

"…I hope next year the football team comes back full force." Tyler was saying to Matt, but Matt's head seemed like it was somewhere else tonight. Elena found it hard to be sympathetic to both sides. Matt was being a jerk, Caroline was being… Caroline. Given Elena admired how much Caroline liked Matt, she knew that look in her eyes all too well. It was the same look she used to give Matt when she was unsure of what the future held for them. But Matt, his look was drained of love. There wasn't an ounce of a honeymoon phase left in him. It was like the vampire's got his heart instead of the blood. Elena expected to see the longing in Matt's eyes that she used to see when they broke up.

It just wasn't there.

"Yeah me too, I can't wait to go over some of the new routines." Caroline said, I mean it's exciting enough that I have all the extra energy. Now, I can really use it for something I love without worrying about getting hurt or twisting my body the wrong way."

Damon walked into the war, gracefully taking off his leather jacket. His eyes immediately locked with her own and she just couldn't pull herself away until she saw Stefan. It was strange that Damon was just walking in, he'd spent several minutes outside and was just now coming in.

_Stefan's the one you love, _she told herself, _and this is just a phase in every girl's life when they want the bad boy. It'll be over soon. _

The way she coached herself was like she was getting a shot, or recovering from an illness. It wasn't at all the way emotions should be rationalized. That's what Elena does though, she accusing Damon of shutting people out but she's blocking him from her mind and from her heart. She's got an army set up there- her main soldiers were Stefan, Caroline, and Jeremy and she didn't know what to do. Advice columnist would say that's love, and that's life. Love is confusing, love is this emotion where you can't stop thinking about someone and everything you do- you want to do with them because you can't see your life without them. She felt that for Stefan at one point, and she still did. She wasn't trying to get any lines crossed, she loved Stefan.

But she was tired of saying the same thing every time her love for Stefan was questioned. He came into her life at a hard time- like a rebound from her parent's death. What did that mean? God, she was so confused all the time when both of them were in a room with her. Stefan didn't want her to have that relationship with Damon- he wanted to be the first call when she got hurt. Damon wanted to be the first call for she was hurt too. Elena just wanted to choose, but how could she when the stakes were so high?

Stefan walked over to the table, while Damon lingered then made his way to the bar. Suddenly, Elena pushed back her scattered emotions and decided tonight was about high school, and being human even though most of the people she happened to be with weren't human. At all.

"What took you so long?" Elena asked Stefan with a laugh, "You were supposed to be here 20 minutes ago."

"I…I was talking to Damon about a family heirloom I've seemed to misplace." Stefan said quickly, avoiding eye contact. He looked over to the bar, and Elena's gaze followed his. He was looking at Damon with his threatening look.

"What are you not telling me?" Elena whispered.

"Nothing, it's nothing." Stefan smiled at her, "Let's try to have a good time tonight."


	2. Chapter 2

Chapter 2:

Elena lingered behind her friends as they walked to the red checkered sheet in the perfect location to watch the slideshow, the mayor was kindly holding it for Tyler and the rest of the group. "Damon…" She said as he came behind her, "Where was he?" Elena watched how he leaned his head to the side, and studied her with that soul searching look in his beautiful blue eyes. His facial features had turned soft due to the fact he was not being guarded around her at the moment. She couldn't help but notice how light his features were but his eyebrows kept their much serious tone as if he was debating something important inside his head. "Damon." She repeated warning him in case he got the urge to lie to her.

"I don't know." Damon said seeming to tell the truth, Elena wanted to believe him but something was blocking that belief. It was the hesitation, and the pause along with the evaluation of her current emotions- Damon wasn't being a hundred percent truthful with her and his face gave it all away. Elena looked at him with her lips pursed tightly- she wanted to say something but instead she let it go until she could control the sudden rage. It didn't work very long.

"Don't lie to me!" Elena said slightly louder than she should have, but her eyes met his in a determined way. She grasped his hand tightly in her own as a way of telling him that he would not regret his choice. "You know more than you're telling me."

Damon sighed, rolling his eyes while quickly shifting his head to the other side. "Elena, I don't know." He repeated as he swung both of his arms out to his side in defense. Then he said quietly, "I don't want to know...I saw him coming out from the Bed and Breakfast. He might have been meeting someone, or he might have stopped in for something. Either way, it's not my place." He pointed off towards the old Inn that was refurnished into a Bed and Breakfast. Elena's face dropped as a thousand suspicious thoughts ran through her head. Would Damon lie to her to make himself look better? But the answer to that was a quick and confident _No. _Damon would never hurt Elena for his own personal gain. He knew she would hate him if he did.

"But you're going to find out." Elena stated, of course he was going to find out. She let go of his hand as she felt a fiery stare focus on her back. It was Caroline or Stefan- all she knew was someone happened to be watching her. "Thank you." She said before she turned and walk to her friends, she stopped mid-stride and glanced back at him. "Aren't you coming?" Her eyes reflected innocent curiosity. Her heart wanted him to take a step closer to her, her heart needed it. She needed Damon to prove that he cared so she could decide what she was going to do.

He smirked at her, returning a witty comment. "You just can't live without me, can you?" He put his arm around her shoulders, but she quickly pushed it away. It was her natural reflex, acting like she didn't enjoy the attention he was so willing to give her every second of every day.

Elena took her rightful seat by Stefan, while Damon took an open space by her. He leaned over and whispered in her ear, "That last time I was having a picnic in the park they wrote a song about it." He continued on, "World peace, Marijuana and a thousand girls just wanting to throw themselves at anything that looked like me."

Elena giggled, actually giggled at the joke he was making- no matter how poorly it was executed or how censored it probably was. "Are you trying to tell me you were for world peace?"

"No Elena," Damon said almost seductively, "I'm trying to tell you I enjoy picnics- plenty of… snack food." He winked at her.

"All Damon liked about the picnics were the endless supply of stoned hippies he could drain of blood." Stefan said coldly, "Please Elena, don't encourage him."

The Mayor to her post at the podium and started her speech, "This year Mystic Falls has experienced many great losses, much more than any town and its citizens should ever have to. Yet, all of you have found a way to wake up and make memories with the people you love and for that you are beyond strong. This evening will be the first showing of the junior and senior slideshow. Thank you all for showing up and supporting Mystic Falls High School." Everyone clapped at the Mayor's short but powerful speech and proceeded to watch the opening titles of the slideshow.

The beginning of the slideshow introduce a few seniors, and a list of those graduating this year. Elena yawned after not being able to contain it. "I'm sorry" She told Stefan who looked at her with question. "I stayed up too late." She assured him.

"Yeah sorry about that." Damon joked once more, "All you had to do was ask me to leave."

"That's enough Damon!" Stefan nearly growled at him, Damon held his hands up in defense. "Do you think he's funny, Elena?"

"No, of course not…" Elena looked back at Damon. "I'm sorry Stefan, I'm just trying to have fun." She yawned once more, and Stefan looked at her. Surly, she started to drift away. She felt herself leaning over, but she lost focus on which direction she was going. Her thoughts were scattered, every time she opened her eyes she saw different pictures, then her eyes started to play tricks on her. Randomizing the pixels until the picture didn't make sense, then her vision blurred and she fell back asleep. She felt complete comfort against warm skin.

Then a cold hand shook her awake, "Elena." She heard Stefan's voice through the blackness of a nonexistent dream. "Elena get up, it's time to go."

She opened her eyes to see Stefan above her, as she moved she felt the stickiness of leather against her skin. "Sorry." She told Damon as she got up, "I didn't mean to fall asleep on you." _You idiot, way to mask your feelings Elena! He's not the one you end up with! _"I'll see you around." She told him, raising her eyebrows as she spoke.

As Elena and Stefan walked down the street, Stefan stopped. "What's going on?" He asked her, "Hm?" He made that sound as he shoved his hands in his pockets. He looked off in space, ironically towards the Bed and Breakfast he had been at earlier that evening.

Elena knew that her emotions were everywhere, but she wasn't trying to pursue Damon. She was trying to get over the whole bad boy crush. Her heart was just having a hard time accepting that concept. She knew that she would end up with Stefan. Logically, he was the safest and most practical choice. He would never hurt her, or bring an extreme amount of danger into her life on purpose.

"I don't know what you're talking about." Elena said slowly, emphasizing each word with question, "Because it sounds like you're accusing me of something." _Like cheating. _Elena put her hands on her hips.

"Maybe I am." Stefan said, "You know what that's exactly what I'm doing. What is going on with you and Damon?"

"I'm not Katherine, in case you didn't realize that." Elena said, "I'm not sleeping with Damon, I'm not going behind your back with Damon. Nothing is going on with Damon and me."

Stefan laughed humorlessly, "For someone who is so dead-set on not being Katherine, you sure are a lot like her."

"How could you say that to me?" Elena said without hesitation, "How could you look at me and accuse me of something when you lied straight to my face?"

"Exactly, something Katherine would do. Try to turn a situation right around on me. Well guess what? Until you give me an answer- I'm through with this." He pointed back and forth between him and Elena. Elena just looked at him, trying to scoop up a lot of sadness from her heart- there were a few tears coming out of her eyes, and she opened her mouth to speak but nothing came out as he walked away.

"Exactly," Elena repeated. "Something Katherine would do. Try to turn a situation right around on me." Her tone was full of anger.

Her thoughts started to ramble on in an angry rant:

_He wants to act like this is my fault, but it's not. It's his. Or is it? This is my fault…I have feelings for Damon and I won't admit that. Maybe I should…would that change anything? No, no… He turned his lie back around on me. That's why he's angry. He probably heard me talking to Damon… He knows I'm onto him. He wants me to look like the jerk… _

"Elena…Are you okay?" Damon asked her, appearing out of nowhere- making her jump. She turned around to stare at him. He touched her face, and wiped away a stray tear. "I don't deserve you…" He whispered. "So don't ruin it with him, he loves you and you love him. I'm just a stepping stone in the Stefan and Elena relationship."

_Don't._

"I'm not the guy girls like you end up with, I'm the guy they date before they end up with guys like Stefan." He continued on, each word was breaking Elena's shell more and more. Her tears started falling more frequent.

_Damon, don't… Don't be so honest with me._

"I'm. A. Monster." He ended his small speech.

Elena shook her head, "Damon, you're not the monster in this situation. I am." She sighed, "Stefan's right, I'm just like Katherine. I can't make up my mind about either of you."

Damon just stood there, "Then I'll make it easy for you Elena. Pick Stefan." His honesty was ripping Elena apart. He clearly didn't view himself within the grasp of salvation, he didn't see himself as good but Elena saw the goodness within him. It was in every speech he gave to her, it was in every joke he made to try to lighten a serious situation. "You'd be crazy to pick me."

"Aren't all the Gilbert's a little crazy?" She pointed out, "I wouldn't be crazy to pick you. I'd be crazy to let you walk home without kissing you tonight because I've wanted to for a really long time and if I'm going to make any type of choice…it's going to be to follow my heart."


End file.
